Advising undergraduate students on how to succeed in their academics, careers, and life is one of the most common practices in higher education. Advising is also something that many institutions struggle to resource or coordinate sufficiently, due to hurdles such as overwhelming caseloads and limited interdepartmental communication, potentially leaving students without needed support on their paths to successful program completion. This research brief compares and contrasts the experiences of two institutions, Webster University and West Virginia State University (WVSU), in piloting a new advising technology.